In the second half of their discussion on ambition, Dan Sullivan and Steve Krein explore how ambition can remain fresh and exciting at every stage of the entrepreneurial journey. They reveal why measuring progress correctly, creatively managing your time, and building personalized systems help you stay motivated, resilient, and focused on a bigger future.

Show Notes:

Ambition means always having a future that feels bigger and more exciting than your past.

The urge to see how far you can really go unlocks an endless cycle of growth and new achievements.

Progress is best measured by looking back at how far you’ve come, not by comparing against some distant, moving target.

Focusing only on what’s next makes it hard to appreciate the real gains you’ve already made.​

Most Strategic Coach® tools are created to solve the feeling of being stuck or falling short.​

Celebrating even small wins keeps momentum strong, and progress doesn’t have to take forever.​

Structuring your time around a handful of priorities, like five tasks over three days, offers creative flexibility and less pressure.​

Every thriving entrepreneur has built their own time system that fits how they work best.​

Working nonstop isn’t a badge of honor; you’re better off building in time for rest and recovery.​

Resources:

The Gap And The Gain by Dan Sullivan with Dr. Benjamin Hardy

The Impact Filter™

Time Management Strategies For Entrepreneurs (Effective Strategies Only)

The Positive Focus®

Primal Intelligence by Angus Fletcher

Always More Ambitious by Dan Sullivan

What if your ambition isn't a finite resource you're destined to deplete? Dan Sullivan introduces a transformative idea that ambition is a muscle that strengthens with use. Learn how to grow this core capability at any age, why contentment and ambition can coexist, and how to build a collaborative environment that fuels your future.

Show Notes:

Ambition is a fundamental capability that enables all other capabilities.

Many people misunderstand ambition, thinking it’s a natural gift (and a finite resource) rather than a muscle to develop.

It requires significant energy to maintain your ambition entirely on your own.

Being surrounded by ambitious people fuels greater ambition and makes big thinking easier.

Contentment and ambition are not opposites; both can be present when personal growth is the focus.

Social norms often discourage ambition after 60, but real impact happens when entrepreneurs defy those expectations.

Transitioning from solo effort to teamwork, then to external collaboration, marks an entrepreneur’s real growth journey.

Strategic Coach® is where already ambitious entrepreneurs become even more ambitious.

Collaborative ambition multiplies results and helps entrepreneurs expand their reach by combining capabilities.

The Strategic Coach community supports entrepreneurs by enabling collaborative, not competitive, growth.

Facing headwinds around ambition is normal; Strategic Coach offers tools to overcome them and extend longevity in business.

Your “here” is always expanding into “there”—ambitious entrepreneurs never settle at a finish line.

Resources:

How To Foster A Longevity Mindset & Reap The Benefits

Who Not How by Dan Sullivan with Dr. Benjamin Hardy

Free Zone Frontier by Dan Sullivan

Unique Ability®

The importance of intellectual property is undeniable, but not everyone knows as much about their own IP situation as they should. Dan Sullivan and Steve Krein chat with Keegan Caldwell, the founder of an intellectual property law firm, who explains how IP law can benefit entrepreneurs beyond just protecting their creations.

Show Notes:

• An entrepreneur’s mindset is crucial because that’s what determines their behavior.
• Never fall in love with your creation until check writers fall in love with your creation.
• There’s value in long-term growth companies, but they need to have the revenue to support their plans.
• If you have a concept or idea that’s differentiating you in the marketplace, you likely have some IP that's worth discussing and protecting.
• In addition to protecting your innovation, IP can be used to create licensing and fundraising opportunities to drive up value for an IPO or an acquisition.
• Many companies don’t even think about intellectual property issues until they’re some ways down the road.
• One way to show you really believe in a technology you’ve created is to take the initiative to protect it.

Resources:

Learn about Keegan Caldwell

Who Not How by Dan Sullivan and Ben Hardy

How To Live To 156 by Dan Sullivan

The Gap And The Gain by Dan Sullivan and Ben Hardy

Why do some companies continually grow while most fail? You need more than a great idea; you need to surround yourself with others who are thinking the same way. Dan Sullivan and Steve Krein discuss the successes of Steve’s unique, collaborative StartUp Health network, the mindsets entrepreneurs need in order to achieve the greatest success, and the things they do that most entrepreneurs won’t even think about. 

• Medical breakthroughs are happening at such a fast rate that the most knowledgeable person really only knows how ignorant they are.
• “Free Zone” collaborations aren’t about the money that’s exchanged.
• True collaboration bypasses a lot of problems entrepreneurs normally think about because there’s no competition.
• There’s probably no industry on the planet that has less collaboration than health care.
• It can be difficult to maintain a transformative mindset when you’re surrounded by resistance to transformation.
• If you’re working at effecting change over the long term, you need to have a long-term view to feel good waking up every day.
• There are entrepreneurs who are coachable and open to the idea of lifelong learning, and there are entrepreneurs who aren’t there yet.
• Even at their most competitive, entrepreneurs are more collaborative than people who aren’t in the entrepreneurial marketplace.
• Real intelligence isn’t what your individual brain does; it’s how your brain accesses the brains of other people.

Resources:

Unique Ability®

The Strategic Coach® Program

What Is Rugged Individualism? And Why You Might Be Guilty Of It

Innovations in the realm of age reversal are accelerating. Getting physically younger while getting older in years is a real possibility. In this episode, Dan Sullivan and Steve Krein explain the advances, discuss what’s needed for further breakthroughs, and share why age reversal developments are critical for entrepreneurs to be preparing for. 

Show Notes:

• Many entrepreneurs retire out of social or societal expectations.
• Setting a goal that might seem crazy serves as a magnet for what you need and as a repellent for what you don’t.
• You treat your remaining years differently depending on when you think you’re going to die.
• Thinking about your legacy means you’re thinking about being gone.
• There’s the expectation in society that once you turn 65 or 70, you don’t take on anything new.
• The solution won’t be possible if you don’t have the goal.
• Medicine is going to become the fastest growing industry in the United States.
• There are thousands of solutions that need to be worked on to enable true age reversal.
• There's been an incredible drop-off in venture capital funding of all areas except health and medicine.
• American progress in all areas is driven by adventuresome consumers.
• Mission alignment is the single most important predictor of success in long-term health-related entrepreneurial ventures.

Resources:

The Strategic Coach® Signature Program

Learn more about Steven Krein at StartUp Health

My Plan For Living To 156 by Dan Sullivan

Dan Sullivan and Steve Krein delve into the power of the “When Are You Great?” tool, discussing how it serves as a crucial planning aid and a potent marketing resource. Using real-world examples, they explore the implications for crafting compelling offers, narrating impactful stories, and leveraging a marketer’s secret weapon.

Show Notes:

• To figure out what gets talked about, you have to combine everything you’re telling with everything you’re being told.
• You share when you’re good because you have competition. Others share when you’re great because they don’t think you have any competition.
• Saying when you’re good is trying to make a convincing argument. Being told when you’re great is your compelling offer.
• How you're making people feel transcends what you do for them.
• Your messaging should include both what you do and what happens when someone participates.
• Measuring impact is hard in the short term, but unavoidable in the long term.

Resources:

The Four Freedoms

The Self-Managing Company by Dan Sullivan

The Strategic Coach Entrepreneurial Time System®

The End of the World is Just the Beginning by Peter Zeihan

In one of our most popular episodes, Steve and Dan revisit why there’s a big difference between convincing someone with an argument and compelling them to take action with an offer. And in the market world where we all live, people don’t want to be convinced—they want to be compelled.

Show Notes:

A convincing argument is about the speaker, but a compelling offer is about the listener.

In the education system, you convince someone with your argument, but it doesn’t get them to take any action.

Characteristics of a compelling offer are that it happens very fast, and the clients don’t have to do much work to get it.

Humans aren’t computers, but meaning makers.

The basis of a compelling offer is that everyone is thinking in one direction, and then you present a message that changes the way they’re thinking about things.

Data is what you need to make an argument convincing.

Some people see situations in black and white (it happened or it didn’t happen), and don’t see the progress being made.

When you make a compelling offer, people want to be involved regardless of when the success will come. 

When someone is facing a new experience, it will be a good experience if they have something new as a solution, and a bad experience if they don’t.

Resources:

Deep D.O.S. Innovation by Dan Sullivan

You Are Not a Computer by Dan Sullivan

Dan Sullivan and Steve Krein explore the powerful 4 x 4 Casting Tool™, which can transform how you integrate new team members into your company—and galvanize your current team members to take ownership of their roles. Discover how treating your company like a theater project ensures you have the right people in the right roles for maximum impact.

Show Notes:

• An entrepreneur's primary job is to push things forward, not get stuck in bureaucratic processes.
• The least productive thing you can say to your team as an entrepreneur is, “I’m unhappy with you, but I’m not going to tell you why.”
• The 4 x 4 Casting Tool tells people how you expect them to show up, how they show progress in terms of getting things done, how they can be a hero to you, and how they can drive you crazy.
• It also empowers team members to take ownership of their roles within the company.
• When someone new joins your team, it's your job to tell them what the game plan is and what's expected of them. People can’t read your mind.
• Traditional job descriptions are impersonal and technical, and they fail to capture the nuanced working relationships that can (and should) develop in a growth-focused team.
• Having a Self-Managing Company® means that every team member is managing their constant growth and contributions in the company.
• You can’t complain and create at the same time.
• Remote work has fundamentally changed team dynamics, and it will take more effort to ensure team members feel connected to each other—and your vision.

Resources:

Anything And Everything Podcast

What Is A Self-Managing Company®?

Unique Ability®

Why Work Sucks and How to Fix It: The Results-Only Revolution by Cali Ressler and Jody Thompson

Entrepreneurial Operating System®

Who Not How by Dan Sullivan and Dr. Benjamin Hardy

The Gap And The Gain by Dan Sullivan and Dr. Benjamin Hardy

10x Is Easier Than 2x by Dan Sullivan and Dr. Benjamin Hardy

Your Business Is A Theater Production: Your Back Stage Shouldn’t Show On The Front Stage

The Impact Filter™

The Great Crossover® by Dan Sullivan

Dan Sullivan and Steve Krein discuss the Free Zone Frontier® and the StartUp Health programs. They both believe it’s crucial to have the right people in the room, sharing their experiences and collaborating. Connecting like this with a community of ambitious, calm entrepreneurs makes it possible to experience five years’ progress in three months.

Show Notes:

• What happens backstage is more magical than what’s seen on stage.
• Gutenberg's invention of the printing press was a revolution that led people to start having conversations with themselves.
• Fifty years into the microchip revolution, a “team consciousness” is emerging.
• In any group, the individuals’ mindsets are the most important factor.
• Entrepreneurs tend to be isolated. In Steve’s StartUp Health and Dan’s Free Zone Frontier, it’s understood that you can't go it alone.
• Belonging to a community of confident, ambitious, and calm peers helps entrepreneurs make the next leap.
• In the Free Zone Frontier, entrepreneurs report making five years’ progress in three months.
• Dan predicts that technology will increasingly go “maximum global,” and that people will stay closer to home and focus on their own communities.

Resources:

Learn more about Steve’s company, StartUp Health

The Strategic Coach® Signature Program

Ever wondered what the success formula is for top entrepreneurs? Dan Sullivan and Steve Krein discuss “The 25-Year Framework” and how it benefits entrepreneurs by helping them prioritize their biggest goals and measure progress every quarter. They explain how having a quarterly rhythm can be transformational, and provide insights into how to achieve long-term goals, adapt to advancements in technology, and overcome crises in the marketplace.

Show Notes:

• Measuring your past progress and planning out the next quarter, every quarter, helps simplify and multiply your efforts.
• This kind of self-accountability and measurement allows for compounding results.
• Growth entrepreneurs must engage in quarterly reflection to achieve their goals.
• Entrepreneurs who treat every quarter in business as a 90-day period of progress, recalibrating and staying committed to their goals, are much more likely to weather market disruptions (such as a global pandemic) and will fare better in the long run.
• Quarterly review and recalibration are essential for achieving not only professional goals, but personal ones as well, and help you build meaningful relationships.
• Your social circle can either support or obstruct your goals. Curate it regularly.
• Avoid making major decisions on Friday afternoons. Everything feels much bigger and scarier when you’re tired from the week, whereas you have a fresh perspective and more energy at the start of the week.
• To reach your quarterly goals, you must commit to weekly improvements.

Resources:

The 25-Year Framework by Dan Sullivan

The Strategic Coach® Program

StartUp Health

Free Zone Frontier by Dan Sullivan

Unique Ability®

The Entrepreneur’s Guide To Time Management (Free Days™)